Mestilbol

{{Short description|Chemical compound}}

{{Drugbox

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| IUPAC_name = 4-[(E)-4-(4-methoxyphenyl)hex-3-en-3-yl]phenol

| image = Mestilbol.svg

| width = 250px

| tradename = Monomestro, Monomestrol

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| class = Nonsteroidal estrogen; Estrogen ether

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| CAS_number_Ref =

| CAS_number = 18839-90-2

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| PubChem = 3032340

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| ChemSpiderID = 2297337

| UNII = N44U12UW5N

| KEGG =

| ChEBI = 34702

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| synonyms = Monomethylstilbestrol; Diethylstilbestrol monomethyl ether

| C=19 | H=22 | O=2

| SMILES = CCC(=C(CC)C1=CC=C(C=C1)OC)C2=CC=C(C=C2)O

| StdInChI_Ref =

| StdInChI = 1S/C19H22O2/c1-4-18(14-6-10-16(20)11-7-14)19(5-2)15-8-12-17(21-3)13-9-15/h6-13,20H,4-5H2,1-3H3/b19-18+

| StdInChIKey_Ref =

| StdInChIKey = CKMDPZMWUZDKAI-VHEBQXMUSA-N

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Mestilbol (brand name Monomestro or Monomestrol), also known as diethylstilbestrol monomethyl ether, is a synthetic nonsteroidal estrogen of the stilbestrol group related to diethylstilbestrol.{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA396|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|page=396}}{{cite book| vauthors = Negwer M |title=Organic-chemical drugs and their synonyms: (an international survey)|url=https://books.google.com/books?id=k6fwAAAAMAAJ&q=%22monomestro%22|year=1987|publisher=VCH Publishers|isbn=978-0-89573-552-2|page=923}}{{cite book|author=Council on Drugs (American Medical Association)|title=New and Nonofficial Drugs|url=https://books.google.com/books?id=0n4YAQAAIAAJ&q=%22Monomestrol%22|year=1955|publisher=Lippincott|pages=419–420}} It was developed by Wallace & Tiernan Company, patented in 1940,{{cite patent | country = US | number = 2385468 | title = Monoalkyl ethers of diethylstilboestrol| inventor = Emmet RE | assign1 = US Filter Wallace and Tiernan Inc | gdate = 25 September 1945

}} and introduced for medical use in the 1940s,{{cite journal| vauthors = Sevringhaus EL |title=Therapy of the Patient in the Menopause: Endocrine Methods|journal=The Journal of Clinical Endocrinology & Metabolism|volume=4|issue=12|year=1944|pages=597–604|issn=0021-972X|doi=10.1210/jcem-4-12-597}} but is now no longer marketed. Mestilbol was available both as oral tablets and in oil for intramuscular injection. The drug is gradually demethylated in the body into diethylstilbestrol and hence is a prodrug of diethylstilbestrol.{{cite book|title=Annales de Bourgogne|url=https://books.google.com/books?id=JYlNAAAAMAAJ|year=1940|publisher=Centre d'études bourguignonnes}} Mestilbol is a highly active estrogen,{{cite book|title=Postgraduate Medicine|url=https://books.google.com/books?id=Cq7yAAAAMAAJ|year=1949|publisher=McGraw-Hill|page=347}} although somewhat less so than diethylstilbestrol,{{cite book| vauthors = Russell La Fayette C, Loeb RL |title=A Textbook of Medicine|url=https://books.google.com/books?id=QUtBAAAAYAAJ|year=1951|publisher=Saunders}} but is longer-lasting in comparison.{{cite book| vauthors = Salter WT |title=A Textbook of Pharmacology: Principles and Application of Pharmacology to the Practice of Medicine|url=https://books.google.com/books?id=rFzZT45hG6kC|year=1952|publisher=Saunders}}